NPASS Compound

Structure

NPC470345 OpenBabel07101718322D 32 35 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -1.1499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0686 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 2 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 27 1 0 0 0 0 8 28 1 0 0 0 0 9 28 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 16 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 17 1 1 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 22 29 1 6 0 0 0 23 27 1 0 0 0 0 23 30 2 0 0 0 0 24 28 1 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 25 31 2 0 0 0 0 29 10 1 1 0 0 0 29 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.33
Volume:	491.739
LogP:	7.163
LogD:	5.197
LogS:	-5.995
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	5.027
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953
MDCK Permeability:	1.2163116480223835e-05
Pgp-inhibitor:	0.934
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	91.24026489257812%
Volume Distribution (VD):	1.982
Pgp-substrate:	6.11601448059082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.648
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.621
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	7.044
Half-life (T1/2):	0.024

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.56
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.45
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.063
Carcinogencity:	0.176
Eye Corrosion:	0.009
Eye Irritation:	0.028
Respiratory Toxicity:	0.986

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC470345

Natural Product ID:	NPC470345
*Common Name:**	Rel-Myrtucommulone K
IUPAC Name:	(8R,8aS,9S,10aS)-8-(2,2-dimethylcyclopentyl)-2,2,4,4,10a-pentamethyl-7-methylidene-9-propan-2-yl-6,8,8a,9-tetrahydro-5H-xanthene-1,3-dione
Synonyms:	Rel-Myrtucommulone K
Standard InCHIKey:	TUBFXKZFEGFKBF-URAKOGNMSA-N
Standard InCHI:	InChI=1S/C29H44O3/c1-16(2)19-21-23(30)27(6,7)25(31)28(8,9)24(21)32-29(10)15-13-17(3)20(22(19)29)18-12-11-14-26(18,4)5/h16,18-20,22H,3,11-15H2,1-2,4-10H3/t18?,19-,20-,22-,29+/m1/s1
SMILES:	CC(C)C1C2C(C(=C)CCC2(OC3=C1C(=O)C(C(=O)C3(C)C)(C)C)C)C4CCCC4(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011677
PubChem CID:	57333286
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4570	Myrtus communis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499325]
NPO4570	Myrtus communis	Species	Myrtaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22276775]
NPO4570	Myrtus communis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell Line	MT4	Homo sapiens	IC50	>	100000.0	nM	PMID[534675]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	560000.0	nM	PMID[534675]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC470345 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	1584
0.2-0.3	6884
0.3-0.4	13161
0.4-0.5	10380
0.5-0.6	6881
0.6-0.7	3185
0.7-0.8	397
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8391	Intermediate Similarity	NPC470346
0.8276	Intermediate Similarity	NPC478245
0.8222	Intermediate Similarity	NPC213636
0.8222	Intermediate Similarity	NPC280592
0.8222	Intermediate Similarity	NPC478258
0.8222	Intermediate Similarity	NPC253177
0.8222	Intermediate Similarity	NPC478257
0.8132	Intermediate Similarity	NPC296114
0.8132	Intermediate Similarity	NPC471329
0.8095	Intermediate Similarity	NPC478247
0.8095	Intermediate Similarity	NPC469996
0.8095	Intermediate Similarity	NPC478246
0.809	Intermediate Similarity	NPC38885
0.8022	Intermediate Similarity	NPC223093
0.7895	Intermediate Similarity	NPC477268
0.7895	Intermediate Similarity	NPC477267
0.7895	Intermediate Similarity	NPC472690
0.7895	Intermediate Similarity	NPC472689
0.7889	Intermediate Similarity	NPC471728
0.7816	Intermediate Similarity	NPC478262
0.7816	Intermediate Similarity	NPC472684
0.7816	Intermediate Similarity	NPC44963
0.7802	Intermediate Similarity	NPC143767
0.7802	Intermediate Similarity	NPC131470
0.7802	Intermediate Similarity	NPC478259
0.7802	Intermediate Similarity	NPC478261
0.7802	Intermediate Similarity	NPC478260
0.7789	Intermediate Similarity	NPC472734
0.7789	Intermediate Similarity	NPC472733
0.7727	Intermediate Similarity	NPC70479
0.7717	Intermediate Similarity	NPC275740
0.7717	Intermediate Similarity	NPC86319
0.7708	Intermediate Similarity	NPC472732
0.7708	Intermediate Similarity	NPC472731
0.7708	Intermediate Similarity	NPC27105
0.7692	Intermediate Similarity	NPC30421
0.7667	Intermediate Similarity	NPC470574
0.7634	Intermediate Similarity	NPC183283
0.7629	Intermediate Similarity	NPC472730
0.7629	Intermediate Similarity	NPC203388
0.7629	Intermediate Similarity	NPC471330
0.7629	Intermediate Similarity	NPC472729
0.7629	Intermediate Similarity	NPC99657
0.7629	Intermediate Similarity	NPC153776
0.7629	Intermediate Similarity	NPC472687
0.7629	Intermediate Similarity	NPC471331
0.7629	Intermediate Similarity	NPC177680
0.7614	Intermediate Similarity	NPC189237
0.7609	Intermediate Similarity	NPC143025
0.7609	Intermediate Similarity	NPC328539
0.7609	Intermediate Similarity	NPC471724
0.7582	Intermediate Similarity	NPC195640
0.7582	Intermediate Similarity	NPC477479
0.7582	Intermediate Similarity	NPC477478
0.7582	Intermediate Similarity	NPC72133
0.7553	Intermediate Similarity	NPC478243
0.7553	Intermediate Similarity	NPC63748
0.7553	Intermediate Similarity	NPC218301
0.7553	Intermediate Similarity	NPC478244
0.7551	Intermediate Similarity	NPC472727
0.7551	Intermediate Similarity	NPC472728
0.7528	Intermediate Similarity	NPC321289
0.7528	Intermediate Similarity	NPC477269
0.7528	Intermediate Similarity	NPC129080
0.7528	Intermediate Similarity	NPC476935
0.7528	Intermediate Similarity	NPC327969
0.7528	Intermediate Similarity	NPC477271
0.7528	Intermediate Similarity	NPC193347
0.7528	Intermediate Similarity	NPC477270
0.7527	Intermediate Similarity	NPC50070
0.7527	Intermediate Similarity	NPC305039
0.7527	Intermediate Similarity	NPC473039
0.75	Intermediate Similarity	NPC36321
0.75	Intermediate Similarity	NPC259286
0.75	Intermediate Similarity	NPC317586
0.75	Intermediate Similarity	NPC470016
0.7474	Intermediate Similarity	NPC79117
0.7474	Intermediate Similarity	NPC69454
0.7474	Intermediate Similarity	NPC474807
0.7473	Intermediate Similarity	NPC469948
0.7473	Intermediate Similarity	NPC323765
0.7471	Intermediate Similarity	NPC23778
0.7444	Intermediate Similarity	NPC477373
0.7423	Intermediate Similarity	NPC21681
0.7423	Intermediate Similarity	NPC472675
0.7423	Intermediate Similarity	NPC249954
0.7419	Intermediate Similarity	NPC471722
0.7419	Intermediate Similarity	NPC53911
0.7419	Intermediate Similarity	NPC80335
0.7416	Intermediate Similarity	NPC477372
0.7416	Intermediate Similarity	NPC474085
0.7416	Intermediate Similarity	NPC473217
0.7416	Intermediate Similarity	NPC475665
0.74	Intermediate Similarity	NPC163249
0.7396	Intermediate Similarity	NPC473435
0.7396	Intermediate Similarity	NPC471078
0.7396	Intermediate Similarity	NPC473431
0.7396	Intermediate Similarity	NPC166906
0.7396	Intermediate Similarity	NPC473280
0.7386	Intermediate Similarity	NPC215843
0.7374	Intermediate Similarity	NPC112167
0.7368	Intermediate Similarity	NPC190442
0.7368	Intermediate Similarity	NPC185936
0.7368	Intermediate Similarity	NPC472975
0.7368	Intermediate Similarity	NPC168027
0.7368	Intermediate Similarity	NPC248913
0.7363	Intermediate Similarity	NPC144258
0.7363	Intermediate Similarity	NPC109512
0.7363	Intermediate Similarity	NPC251170
0.7363	Intermediate Similarity	NPC85774
0.7363	Intermediate Similarity	NPC320801
0.7363	Intermediate Similarity	NPC214043
0.7363	Intermediate Similarity	NPC473246
0.7356	Intermediate Similarity	NPC472300
0.7349	Intermediate Similarity	NPC139397
0.7347	Intermediate Similarity	NPC23680
0.7347	Intermediate Similarity	NPC151488
0.734	Intermediate Similarity	NPC472688
0.734	Intermediate Similarity	NPC472676
0.734	Intermediate Similarity	NPC472973
0.734	Intermediate Similarity	NPC474570
0.7333	Intermediate Similarity	NPC469325
0.7333	Intermediate Similarity	NPC320514
0.7333	Intermediate Similarity	NPC100297
0.7333	Intermediate Similarity	NPC470813
0.7327	Intermediate Similarity	NPC470954
0.732	Intermediate Similarity	NPC473170
0.7312	Intermediate Similarity	NPC475740
0.7312	Intermediate Similarity	NPC136948
0.7303	Intermediate Similarity	NPC74445
0.7303	Intermediate Similarity	NPC287817
0.7303	Intermediate Similarity	NPC476809
0.7303	Intermediate Similarity	NPC279667
0.73	Intermediate Similarity	NPC168319
0.73	Intermediate Similarity	NPC473514
0.73	Intermediate Similarity	NPC194028
0.7294	Intermediate Similarity	NPC474228
0.7294	Intermediate Similarity	NPC303613
0.7292	Intermediate Similarity	NPC229976
0.7292	Intermediate Similarity	NPC472930
0.7283	Intermediate Similarity	NPC133652
0.7283	Intermediate Similarity	NPC29447
0.7283	Intermediate Similarity	NPC300985
0.7283	Intermediate Similarity	NPC137493
0.7283	Intermediate Similarity	NPC470223
0.7283	Intermediate Similarity	NPC197823
0.7282	Intermediate Similarity	NPC220974
0.7273	Intermediate Similarity	NPC207772
0.7273	Intermediate Similarity	NPC147954
0.7273	Intermediate Similarity	NPC275494
0.7273	Intermediate Similarity	NPC176845
0.7273	Intermediate Similarity	NPC476808
0.7273	Intermediate Similarity	NPC471409
0.7263	Intermediate Similarity	NPC191684
0.7263	Intermediate Similarity	NPC44240
0.7263	Intermediate Similarity	NPC8062
0.7263	Intermediate Similarity	NPC328141
0.7263	Intermediate Similarity	NPC474842
0.7263	Intermediate Similarity	NPC475965
0.7263	Intermediate Similarity	NPC161638
0.7262	Intermediate Similarity	NPC159577
0.7262	Intermediate Similarity	NPC35734
0.7262	Intermediate Similarity	NPC282593
0.7262	Intermediate Similarity	NPC260040
0.7262	Intermediate Similarity	NPC2634
0.7262	Intermediate Similarity	NPC265782
0.7262	Intermediate Similarity	NPC307176
0.7262	Intermediate Similarity	NPC251929
0.7255	Intermediate Similarity	NPC40170
0.7255	Intermediate Similarity	NPC13385
0.7253	Intermediate Similarity	NPC472492
0.7253	Intermediate Similarity	NPC470015
0.7253	Intermediate Similarity	NPC470047
0.7253	Intermediate Similarity	NPC271784
0.7253	Intermediate Similarity	NPC168188
0.7253	Intermediate Similarity	NPC64600
0.7253	Intermediate Similarity	NPC470046
0.7245	Intermediate Similarity	NPC96859
0.7245	Intermediate Similarity	NPC328162
0.7245	Intermediate Similarity	NPC151725
0.7245	Intermediate Similarity	NPC106425
0.7245	Intermediate Similarity	NPC120708
0.7245	Intermediate Similarity	NPC328371
0.7245	Intermediate Similarity	NPC111684
0.7245	Intermediate Similarity	NPC305483
0.7245	Intermediate Similarity	NPC122324
0.7245	Intermediate Similarity	NPC58052
0.7228	Intermediate Similarity	NPC119601
0.7228	Intermediate Similarity	NPC308726
0.7222	Intermediate Similarity	NPC201912
0.7222	Intermediate Similarity	NPC38350
0.7222	Intermediate Similarity	NPC476101
0.7222	Intermediate Similarity	NPC147066
0.7216	Intermediate Similarity	NPC114162
0.7216	Intermediate Similarity	NPC212812
0.7216	Intermediate Similarity	NPC469819
0.7216	Intermediate Similarity	NPC184870
0.7209	Intermediate Similarity	NPC469691
0.7209	Intermediate Similarity	NPC167049
0.7209	Intermediate Similarity	NPC309852

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC470345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1942
0.2-0.3	4343
0.3-0.4	1884
0.4-0.5	420
0.5-0.6	151
0.6-0.7	146
0.7-0.8	62
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7778	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD5328	Approved
0.7692	Intermediate Similarity	NPD3573	Approved
0.7582	Intermediate Similarity	NPD6409	Approved
0.7582	Intermediate Similarity	NPD7146	Approved
0.7582	Intermediate Similarity	NPD6684	Approved
0.7582	Intermediate Similarity	NPD5330	Approved
0.7582	Intermediate Similarity	NPD7521	Approved
0.7582	Intermediate Similarity	NPD7334	Approved
0.7553	Intermediate Similarity	NPD6079	Approved
0.7528	Intermediate Similarity	NPD4223	Phase 3
0.7528	Intermediate Similarity	NPD4221	Approved
0.7527	Intermediate Similarity	NPD6904	Approved
0.7527	Intermediate Similarity	NPD6673	Approved
0.7527	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5329	Approved
0.7471	Intermediate Similarity	NPD3617	Approved
0.7419	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5737	Approved
0.7419	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD6903	Approved
0.7419	Intermediate Similarity	NPD5208	Approved
0.7396	Intermediate Similarity	NPD6001	Approved
0.7391	Intermediate Similarity	NPD6098	Approved
0.7391	Intermediate Similarity	NPD3618	Phase 1
0.7368	Intermediate Similarity	NPD6050	Approved
0.7363	Intermediate Similarity	NPD4197	Approved
0.7349	Intermediate Similarity	NPD4137	Phase 3
0.7263	Intermediate Similarity	NPD5692	Phase 3
0.7263	Intermediate Similarity	NPD5207	Approved
0.7262	Intermediate Similarity	NPD4747	Approved
0.7262	Intermediate Similarity	NPD4691	Approved
0.7209	Intermediate Similarity	NPD5733	Approved
0.7204	Intermediate Similarity	NPD5280	Approved
0.7204	Intermediate Similarity	NPD4689	Approved
0.7204	Intermediate Similarity	NPD4138	Approved
0.7204	Intermediate Similarity	NPD4690	Approved
0.7204	Intermediate Similarity	NPD4688	Approved
0.7204	Intermediate Similarity	NPD5690	Phase 2
0.7204	Intermediate Similarity	NPD4693	Phase 3
0.7204	Intermediate Similarity	NPD4694	Approved
0.7204	Intermediate Similarity	NPD5205	Approved
0.7188	Intermediate Similarity	NPD5693	Phase 1
0.7188	Intermediate Similarity	NPD5694	Approved
0.7184	Intermediate Similarity	NPD7128	Approved
0.7184	Intermediate Similarity	NPD6402	Approved
0.7184	Intermediate Similarity	NPD6675	Approved
0.7184	Intermediate Similarity	NPD5739	Approved
0.7176	Intermediate Similarity	NPD5276	Approved
0.7174	Intermediate Similarity	NPD3133	Approved
0.7174	Intermediate Similarity	NPD3665	Phase 1
0.7174	Intermediate Similarity	NPD3666	Approved
0.7172	Intermediate Similarity	NPD4755	Approved
0.7113	Intermediate Similarity	NPD4202	Approved
0.7111	Intermediate Similarity	NPD4695	Discontinued
0.7071	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5221	Approved
0.7071	Intermediate Similarity	NPD4697	Phase 3
0.7071	Intermediate Similarity	NPD5222	Approved
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD7320	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.703	Intermediate Similarity	NPD5285	Approved
0.703	Intermediate Similarity	NPD4696	Approved
0.703	Intermediate Similarity	NPD5286	Approved
0.703	Intermediate Similarity	NPD4700	Approved
0.7021	Intermediate Similarity	NPD5279	Phase 3
0.7019	Intermediate Similarity	NPD6008	Approved
0.7011	Intermediate Similarity	NPD4058	Approved
0.7011	Intermediate Similarity	NPD4687	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6989	Remote Similarity	NPD4786	Approved
0.6981	Remote Similarity	NPD6372	Approved
0.6981	Remote Similarity	NPD6373	Approved
0.6979	Remote Similarity	NPD4753	Phase 2
0.697	Remote Similarity	NPD5695	Phase 3
0.6961	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD3667	Approved
0.6952	Remote Similarity	NPD5701	Approved
0.6952	Remote Similarity	NPD5697	Approved
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.6907	Remote Similarity	NPD4096	Approved
0.6893	Remote Similarity	NPD5226	Approved
0.6893	Remote Similarity	NPD5225	Approved
0.6893	Remote Similarity	NPD5211	Phase 2
0.6893	Remote Similarity	NPD4633	Approved
0.6893	Remote Similarity	NPD5224	Approved
0.6887	Remote Similarity	NPD6011	Approved
0.6882	Remote Similarity	NPD4788	Approved
0.6869	Remote Similarity	NPD7900	Approved
0.6869	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7748	Approved
0.6867	Remote Similarity	NPD7341	Phase 2
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6852	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6848	Remote Similarity	NPD4692	Approved
0.6848	Remote Similarity	NPD4139	Approved
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD5281	Approved
0.6837	Remote Similarity	NPD5284	Approved
0.6827	Remote Similarity	NPD4754	Approved
0.6827	Remote Similarity	NPD5174	Approved
0.6827	Remote Similarity	NPD5175	Approved
0.6824	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6813	Remote Similarity	NPD4195	Approved
0.6809	Remote Similarity	NPD3668	Phase 3
0.68	Remote Similarity	NPD5654	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6789	Remote Similarity	NPD6882	Approved
0.6786	Remote Similarity	NPD7331	Phase 2
0.6768	Remote Similarity	NPD6399	Phase 3
0.6765	Remote Similarity	NPD5696	Approved
0.6762	Remote Similarity	NPD5141	Approved
0.6759	Remote Similarity	NPD4634	Approved
0.6701	Remote Similarity	NPD4518	Approved
0.6698	Remote Similarity	NPD4768	Approved
0.6698	Remote Similarity	NPD4767	Approved
0.6696	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD7902	Approved
0.6634	Remote Similarity	NPD4629	Approved
0.6634	Remote Similarity	NPD5210	Approved
0.66	Remote Similarity	NPD5133	Approved
0.6596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4730	Approved
0.6574	Remote Similarity	NPD4729	Approved
0.6574	Remote Similarity	NPD5128	Approved
0.6562	Remote Similarity	NPD1694	Approved
0.6552	Remote Similarity	NPD6370	Approved
0.6522	Remote Similarity	NPD6319	Approved
0.6491	Remote Similarity	NPD6335	Approved
0.6481	Remote Similarity	NPD6614	Approved
0.6466	Remote Similarity	NPD6016	Approved
0.6466	Remote Similarity	NPD6015	Approved
0.6465	Remote Similarity	NPD6101	Approved
0.6465	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6868	Approved
0.646	Remote Similarity	NPD6274	Approved
0.6455	Remote Similarity	NPD5135	Approved
0.6455	Remote Similarity	NPD5248	Approved
0.6455	Remote Similarity	NPD5249	Phase 3
0.6455	Remote Similarity	NPD5250	Approved
0.6455	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5247	Approved
0.6455	Remote Similarity	NPD5251	Approved
0.6455	Remote Similarity	NPD5169	Approved
0.6442	Remote Similarity	NPD7638	Approved
0.6441	Remote Similarity	NPD7492	Approved
0.6435	Remote Similarity	NPD7101	Approved
0.6435	Remote Similarity	NPD7100	Approved
0.6429	Remote Similarity	NPD4632	Approved
0.6422	Remote Similarity	NPD5168	Approved
0.6421	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5988	Approved
0.6404	Remote Similarity	NPD4243	Approved
0.6404	Remote Similarity	NPD6317	Approved
0.6396	Remote Similarity	NPD5215	Approved
0.6396	Remote Similarity	NPD5216	Approved
0.6396	Remote Similarity	NPD5217	Approved
0.6396	Remote Similarity	NPD5127	Approved
0.6392	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6616	Approved
0.6381	Remote Similarity	NPD7639	Approved
0.6381	Remote Similarity	NPD7640	Approved
0.6373	Remote Similarity	NPD5282	Discontinued
0.6354	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6314	Approved
0.6348	Remote Similarity	NPD6313	Approved
0.6339	Remote Similarity	NPD6053	Discontinued
0.6337	Remote Similarity	NPD8035	Phase 2
0.6337	Remote Similarity	NPD8034	Phase 2
0.6333	Remote Similarity	NPD8293	Discontinued
0.6333	Remote Similarity	NPD7078	Approved
0.633	Remote Similarity	NPD6412	Phase 2
0.6325	Remote Similarity	NPD6909	Approved
0.6325	Remote Similarity	NPD6908	Approved
0.6281	Remote Similarity	NPD7736	Approved
0.6281	Remote Similarity	NPD6033	Approved
0.6264	Remote Similarity	NPD4785	Approved
0.6264	Remote Similarity	NPD4784	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data